Methyl 3beta, 5beta-dihydroxy-b-norcholestane-6beta-carboxylate



United States Patent OH COOCHa 3,129,242 Patented Apr. 14, 1954 The compound of the present invention has anti-inflammatory activity as evidenced by its ability to inhibit the spreading of intradermally injected India Ink. Hydrocortisone, a known and clinically useful anti-inflammatory agent has a similar type of activity in this test.

The compound of the present invention is active on oral, parenteral or topical administration in dosage levels ranging from 0.02 mgs. to 2 grams depending upon vehicle and route of administration. It has useful therapeutic applications in the prevention and treatment of certain allergic and collagen diseases in which inflammation plays a part.

EXAMPLE I Methyl 3 5,5 B-Dihydroxy-B-N 0rcholestane-6 fl- Carboxylate To a solution of 250 mg. (0.546 millimole) of 'Sfiacetoxy-Sfi-hydroxy-B-norcholestane 6 carboxylic acid 5,6-lactone, prepared by the procedure of Boswell (G. A. Boswell et al., Bull. Soc. Chim. France, 1958, 1598), in ml. of methanol was added 1 g. of sodium bicarbonate and the resulting mixture was stirred for 30 hours at room temperature. The mixture was then diluted with 250 ml. of Water, extracted with ether, and the ether extract was washed with water, dried over anhydrous sodium sulfate, and then the ether was evaporated. The residue was crystallized from petroleum ether (15.1. 30-60) to give 160 mg. percent) of methyl 35,55- dihydroxy-B-norcholestane-6B-carboxylate, M.P. 9396 C. One recrystallization gave an analytically pure sample, M1. 9797.5 C., [0t] +35.9 (CI-K31 I claim:

Methyl 3,8,5/3-dihydroxy B norcholestane-6fl-carbox ylate.

References Cited in the file of this patent Groggins: Unit Processes in Organic Synthesis, (New York, 1952), pages 61620.

Boswell et al.: Bull. Soc. Chim., France, 1958, pages 1598-9. 

